75812-87-2

Upstream product

• 89921-31-3 Methyl (+/-)-3-benzamido-4(E)-hexenoate 
• 75812-85-0 Methyl (+/-)-3-amino-4(E)-hexenoate hydrochloride 
• 98-88-4 benzoyl chloride 
• 110079-95-3 lyxo-3-amino-2,3,6-trideoxyhexano-γ-lactone hydrochloride 
• 2396-84-1 (2E,4E)-ethyl hexa-2,4-dienoate 
• 89889-13-4 Methyl (+/-)-3-amino-4(E)-hexenoate 
• 102147-63-7 ((4R,5R,6S)-6-Methyl-2-oxo-5-triethylsilanyloxy-[1,3]oxazinan-4-yl)-acetic acid ethyl ester 
• 102147-61-5 (E)-(4R,5S)-5-Carbamoyloxy-4-triethylsilanyloxy-hex-2-enoic acid ethyl ester 
• 84173-36-4 (E)-ethyl 3-((2RS,3RS)-3-methyloxiran-2-yl) acrylate 
• 102147-61-5 (E)-(4R,5R)-5-Carbamoyloxy-4-triethylsilanyloxy-hex-2-enoic acid ethyl ester 
• 70805-61-7 (E)-(4R,5R)-4,5-Dihydroxy-hex-2-enoic acid ethyl ester 
• 110079-94-2 (3aR,4R,7aR)-4-Methyl-2-trichloromethyl-3a,4,7,7a-tetrahydro-pyrano[4,3-d]oxazol-6-one 
• 110079-91-9 methyl (Z)-3-(N-trichloroacetamido)-4-hexanoate 
• 100689-24-5 (E)-(4R,5S)-5-Carbamoyloxy-4-hydroxy-hex-2-enoic acid ethyl ester 

Downstream Products

• 17016-65-8 N-benzoyl-D,L-ristosamine 
• 75812-89-4 DL-lyxo-3-(Benzoylamino)-2,3,6-trideoxyfuranohexose 5-acetate 
• 17016-65-8 DL-lyxo-3-(Benzoylamino)-2,3,6-trideoxyhexose 
• 75812-88-3 DL-lyxo-3-(Benzoylamino)-2,3,6-trideoxyhexanoic acid γ-lactone acetate 
• 17016-65-8 DL-xylo-3-(Benzoylamino)-2,3,6-trideoxyhexose 
• 75812-88-3 Acetic acid 1-((2S,3R)-3-benzoylamino-5-oxo-tetrahydro-furan-2-yl)-ethyl ester 
• 75812-88-3 Acetic acid 1-((2S,3S)-3-benzoylamino-5-oxo-tetrahydro-furan-2-yl)-ethyl ester 

Relevant academic research and scientific papers

REVERSAL OF DIASTEREOFACIAL SELECTIVITY IN THE INTRAMOLECULAR MICHAEL ADDITION OF δ-CARBAMOYLOXY-α,β-UNSATURATED ESTERS. SYNTHESIS OF N-BENZOYL-D,L-DAUNOSAMINE

Contrary to the precedents, 1,3-anti stereoselection was found in the intramolecular Michael addition of ethyl threo-5-carbamoyloxy-4-trialkylsilyloxy-2-hexenoate to culminate in a synthesis of N-benzoyl-D,L-daunosamine.The antiperiplanar effect due to the group at 4-position was revealed to play a major role in the stereoselection in this type of reactions.N-benzoyl-D,L-3-epidaunosamine was also synthesized by 1,2-syn asymmetric induction.

Stereochemistry of the Epoxidations of Acyclic Allylic Amides. Applications toward the Synthesis of 2,3,6-Trideoxy-3-aminohexoses

The stereochemistry of the epoxidation of several acyclic allylic amides is described.Diastereoselectivity in the (Z)-allylic amide series (compound 1) proved to be dependent both on the amide functionality and epoxidation reagent.The threo epoxide 3 was

DIASTEREOSELECTIVE SYNTHESIS OF N-ACETYL-D,L-ACOSAMINE AND N-BENZOYL-D,L-RISTOSAMINE

N-Acyl derivatives of D,L-acosamine and D,L-ristosamine were synthesized with high stereoselectivity utilizing intramolecular Michael addition of γ- and δ-carbamoyloxy-α,β-unsaturated esters.

Total Synthesis of Optically Active N-Benzoyldaunosamine from an Azetidinone

The azetidinone adduct 5 formed from chlorosulfonyl isocyanate and (E)-1,3-pentadiene was employed as a key intermediate to accomplish an efficient synthesis of optically active LS-N-benzoyldaunosamine (1b).

A Brief Total Synthesis of N-Benzoyl-D,L-daunosamine

A brief regioselective total synthesis of N-benzoyl-D,L-daunosamine from chlorosulfonyl isocyanate (2) and (E)-1,3-pentadiene (1) is described.